N-(1-((1-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide → N-(3-ethyl-1-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79315

Reaction equation

HRID 79315 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([NH:26][C:27]([C:29]4[N:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]5=[N:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:38][CH3:39])=[N:18]2)[CH:13]=[N:12]1)(C(C)(C)C)(C)C>CO.Cl>[CH2:38]([C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:27]([C:29]2[N:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]3=[N:31][CH:30]=2)=[O:28])[N:17]([CH2:16][C:14]2[CH:13]=[N:12][N:11]([CH2:10][CH2:9][OH:8])[CH:15]=2)[N:18]=1)[CH3:39]

Participants

4

Reactant 1

HCID 70814928N-(1-((1-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67260502N-(3-ethyl-1-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 66.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To N-(1-((1-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (15 mg, 0.028 mmol) in MeOH (2 mL) was added concentrated hydrochloric acid (5 drops). The reaction was stirred for 3 hours and concentrated. Silica gel chromatography (DCM/MeOH 10:1) gave the desired product (8 mg). MS (ES+APCI) m/z=430 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-54f2ea8e92124dda85dfc68bcc38bbd0
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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